5 Big Career Risks You Will Regret Not Taking

Someday we’ll all look back and think, “What if? What if I had only done that, or said that, or tried that?”

Like Mark Twain said, “Twenty years from now, you will be more disappointed by the things you didn’t do than by the ones you did do.”

You can always recover, learn, and build from mistakes. But, when you do nothing, that automatically means there is nothing to improve or salvage or discover.

And all you’re left with is, “What if?”

Here are five smart risks you should take before you die. I promise you’ll be glad—if not now, then definitely someday—that you did.

1. Hire or Promote Someone You Probably Shouldn’t Hire or Promote

I took an informal poll of a number of entrepreneur friends. Each said at least one of their most remarkable employees (here’s how to tell if an employee is remarkable) was a person they took a chance on—someone who didn’t have the “right” qualifications, didn’t have the “right” background, was too young or too inexperienced or too new to the industry.

So why did they take a risk on hiring or promoting that person? They had a hunch. They spotted an intangible quality. They loved the person’s attitude or enthusiasm or intelligence or work ethic.

As one CEO told me, “When you hire someone that ticks all the boxes, you get those things. But you rarely get more. Sometimes the risky choice turns out to be the best choice because that person brings qualities you didn’t even know you needed.”

Give an “unusual” candidate a chance. You might get a lot more than you ever hoped, but you’ll never know if you don’t take that risk.

2. Apologize for a Huge Mistake You Made

We’ve all screwed up. There are things we need to apologize for: words, actions, omissions, failure to step up or step in or simply be supportive. Those things happen all the time. We own up and say we’re sorry.

But sometimes we’ve done something so bad, so egregious, so “something” that we don’t say we’re sorry. We’re too embarrassed. Too ashamed. Too mortified. So we run away from the situation, often for years. We wish it would go away.

But it doesn’t. And whenever we think about it, we feel a little worse about ourselves.

Man (or woman) up and say you’re sorry. It may suck. It will suck. You may get yelled at. You may be humiliated.

But you’ll also feel good that you finally stepped up. And you also may repair a friendship or relationship you thought was beyond any hope of recovery, but you’ll never know if you don’t take that risk.

Productive people aren’t braver than others; they just find the strength to keep moving forward. They realize fear is paralyzing, while action creates confidence and self-assurance.

Pick something you’d love to do but are scared to do. Don’t try to get over your fear. Accept that you will be afraid. And then go do it anyway.

I promise it won’t be as bad as you imagined; in fact, you’ll probably realize you were simply scared of the unknown. But you’ll never know if you don’t take that risk.

4. Do One Thing You Dream of Doing That Others Disdain or Ridicule

Bonnie Ware worked in palliative care, spending time with patients who had only a few months to live. Their most common regret was, “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

What other people think—especially people you don’t even know—doesn’t matter. What other people want you to do doesn’t matter.

Maybe you’d like to start a business everyone says you’d be crazy to try. Maybe you’d like to learn to code, but everyone says an old dog can’t learn new professional tricks. Whatever it is you’ve wanted to do but have hesitated because of what other people will think or say, take a chance and do it.

Hear the criticism, take the potshots, endure the laughter or derision or even hostility, and keep measuring yourself by your efforts and your standards.

You may achieve what you want to achieve, or even more, but you’ll never know if you don’t take that risk.

5. Help One Person Simply Because You Can

No matter what you feel you don’t have, there are millions of people who have less than you.

One of them just needs a kind word. Or a little advice. Or a little support.

The next time someone asks you for assistance, take a chance and go a step further. Say, “I can help you with that, but what can I do that would really make a difference? What can I do that would really help you out?”

Do that and you may change another person’s life, but you’ll never know if you don’t take that risk.

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Inc.com is where you can find everything you need to know to start and grow your business now. Inc.com is replete with small business ideas, information, and inspiration, as well as practical advice from those who have done it before.